Substantive orthooxyazo dyestuffs and process of making same.



UNITED saunas PATENT canton EUGEN ANDE'KWERE, HERMANN FRITZSCHE, AND HEINRICH SCHOBEL, 0F BASEL, SWITZERLAND, ASSIGNOES T0 SDGIE'IY 0E GHEMXCAL INDUSTY IN BASLE, 01F

BASEL, SWITZERLAND.

SUBSTANTIVE ORTHOOXYAZO DYESTUEFS AND PROCESS OF MAKING- SAME.

Ho Drawing.

To all whom it may concern:

Be it known that we, EUGEN ANDERWERT, HERMANN FmTzsoHE, and HEINRICH Sono- BEL, all three chemists and citizens of the Swiss Republic and residents of Basel, Switzerland, have invented new Substantive Orthooxyazo Dyestufi's and Processes of Making Same, of which the following is a full, clear, and exact specification.

We have found that valuable new-polyazodyestufls can be obtained by comblning an aromatic orthooxydiazocompound, that is to say the diazoderivative of an orthoaminophenol compound or of an orthoai'ninonaphthol compound or a further diazotized orthooxymonoazodyestufis, with a disazodyestufi containing at least one azodyestufi component able to combine with two diazogroups appertaining to different diazobodies, as for instance resorcinol, metaaminophenol, metaphenylenediamin, 2 7 dioxynaphthalene, an aminonaphthol, 1:8:4-aminonaphtholsulfonic acid, 1: 8: 3: fi-aminonaphtholdisulfonic acid, 1: 8 5-aminonaphtholsulfonic acid, 1 8 l 6-aminonaphtholdisulfonic acid, 2: 5 7 aminonaphtholsulfonic compounds, 2: 5: 1:7 aminonaphtholdisulfonic obtained when the molecule of the dyestuff Specification of Letters Patent.

compounds, etc. The most valuable dyestufis are.

Patented one. '22, 191%..

Application filed fictober 7, 1915. Serial No. 54,513.

acid or 2: 5:1:7 aminonaphtholdisulfonic acid or one of their derivatives. The disazodyestufi" employed as parent materialcan be derived from the tetrazoderivative of benzidin, tolidin, dianisidin, diaminostilbenedisulfonic acid, diaminodiphenylether, di-' aminodiphenylamin, aminobenzojl m phenylenediamin, azooxyanilin, azooxytoluidin, diaminodiphenylurea, diaminodiphenylthiourea, etc.

As 2:5:7 -aminonaphtholsulfonic com pound can be employed the 2:5:7-aminonaphtholsulfonic acid 2: 5 1: 'Z-aminonaphtholdisulfonio acid one of the following derivatives of 2: 5i?- aminonaphtholsulfonic acid:

or one of-the corresponding derivatives of 2 5 1 7-aminonaphtholdisulfonic acid.

' The new dyestufis are intensely colored powders yieldin with concentrated sulfuric 5 acid intensely co ored solutions and dissolvtized and asusual combined with 14.4 kg.

salicylie'acidto an intermediate product; this latter is acidulated with hydrochloric acidtill it shows on Kongo a weakly acid reaction and poured into a, paste of 26 kg. 2:5:7-aminonaphtholmonosulfonic acid, showing also a weakly acid reaction on Kongo. After the combination is effected,- the mass is made alkaline by addition of 20 kg. sodium carbonate, the dyestuff is salted out, separated by filtration and redissolved. To the dyestuff solution are added at first kg. sodium carbonate and afterward the diazo-compound derived from 23.3 kg. or-

thoaminosulfosalicylic acid. The resulting 30 trisazodyestufi isolated as usual dyes unmordanted cotton brown tints.

' vEma/mule 2.'The tetrazode'rivative of 18.4: kg. benzidin is poured into a paste of 50 kg. 2:5:7-aminonaphtholsulfonic acid,

$5 showing a weakly acid reaction on Kongo,

and the excess of mineral acid is gradually neutralized with sodium acetate. vThe disazodyestufi is separated by filtration, dissolved again with 60 kg. sodium carbonate 40 and intothe thus obtained solution is poured the diazoderivative of 37.8 kg. orthoaminophenolsulfonic acid. The trisazodyestufi isolated in the ordinary way yields on unmordantedcotton heliotrope tints.

Emample 3.Into a solution of tetrazodiphenyl derived from 18.4: kg. benzidin is poured a thinspout of a solution of 32 kg. 1 8: 3 6-aminonaphtholdisulfonic acid showing a Weak acid reaction on litmus, care being taken to stir well. After a stirring of about 12 hours the mass is poured into a aeaeee v n 7 solution of 32 kg. 'lz8z2z4-aminonaphtholdisulfonic acid and 30 kg. sodium car-' bonate in a water. The disazodyestuff is salted out, separated by filtration dissolved again with 20 kg. sodium carbonate and into the solution thus obtained is poured a solution of the diazo-compound derivedfrom 15.4 kg. 4: 2: l-nitroaminophenol. The

.trisazodyestufi isolated in the usual manner dyes unmordanted cotton gray-blue tints.

Instead of the diazophenolderivatives indicated in the examples, there can be 'employed the corresponding diazoacidylphenol derivatives which are able to combine more easily, the acidyl-group being split ofi "afterward by saponification'.

. The new dyestufl's are not only suitable for dyeing cotton, wool, silk and mixed goods, straw, wood, paper, ;leather, etc., like the known substantive dyestufis, but also for roductio'n of lakes and as-parent materia s for the production of valuable new derivatives.

What we claim is: I 1. The described process for the manufacture of substantive polyazodyestuffs consisting in combining an aromatic orthooxydiazocompound with. a disazodyestufi' containing at least one azodyestufi component able to combine with two diazogroups appertaining to two different diazobodies.

2. The described process for the manufacture of substantive polyazodyestuffs consisting in combining an aromatic orthooxydiazocompound with a disazodyestufl containing at least one aminonaphtholsulfonic compo nent.

3. The described process for the manufacture of substantive polyazodyestufi's consisting in combining an aromatic orthooxydiazocompound with a disazodyestuff containing a 2:5: 1': 7 -aminonaphthol sulfonic component.

4. The described process for the manufacture of substantive.polyazodyestufis-consistingin'combining an aromatic orthooxydiazocompound with a disazodyestufi' containing a 2: 5 1:7 -aminonaphtholdisul fonic component.

5. As new products the described substantive polyazodyestufii derived from a dismesses azodyestufi and an compound, which powders yielding with concentrated sulfuric acid deep colored solutions and dissolving in water with colorations which are changed intensively on addition of sodium carbonate or of soda lye and dye cotton, wool, silk, mixed goods straw. wood and paper various tints according to the methods used for the known substantive dyestuffs.

6. As new products the described substantive polyazodyestufi's derived from an aromatic orthooxydiazocompound and a disazodyestufi containing at least one aminonaphtholsulfonic component, which constitute deep colored powders yielding with concentrated sulfuric acid deep colored solutions and dissolving in water with colorations which are changed intensively on addition of sodium carbonate or of soda lye and dye cotton, wool, silk, mixed goods, straw, wood and paper various tints according to the methods used for the known substantive dye stufis. c

7. As new products the described substantive polyazodyestufi's derived from an aromatic orthooxydiazocompound and a disazodyestufi' containing a 2:5:7-aminonaphtholsulfonic component, which constitute deep colored powders yielding with concentrated sulfuric acid deep colored solutions and dissolving in Water with colorations which are changed intensively on addition of sodium carbonate or of soda lye and dye cotton, wool, silk, mixed goods, straw, wood and paper various tints according to the methods used for the known substantive dyestufis.

8; As new products the described substantive polyazodyestufi's derived from an aromatic orthooxydiazocompound and a disazodyestufi containing a 2:521:7-aminonaphtholdisulfonic component, which constitute deep colored powders yielding with concentrated sulfuric acid deep colored solutions and dissolving in Water with colorations which are changed intensively on addition of sodium carbonate or of soda lye and dye cotton, wool, silk, mixed goods, straw, wood and paper various tints according to the methods used for the known substantive dyestufi's.

In witness whereof we have hereunto signed our names this 17th day of September, 1915, in the presence of two subscribing witnesses.

Witnesses ARNOLD ZUBER, AMAND Rrrrm. 

